


Matchmaking with Sam and Jess

by orphan_account



Category: Supernatural
Genre: Alternate Universe - High School, F/M, Fluff, M/M, Matchmaking, One Shot, pure fluff
Language: English
Status: Completed
Published: 2014-10-17
Updated: 2014-10-17
Packaged: 2018-02-21 11:46:03
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,586
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/2467121
Author URL: https://archiveofourown.org/users/orphan_account/pseuds/orphan_account
Summary: <blockquote class="userstuff">
              <p>Castiel and Dean are idiots in love and they don't even know - at least, that's what Sam and Jess think.</p>
            </blockquote>





	Matchmaking with Sam and Jess

"Sam, you do know that your brother spent the entire movie making lovey-dovey eyes at Cas, right?" 

Jess was sitting on the floor of the younger Winchester's bedroom, a half-finished history report laid out between them. She was leaning on the side of the bed and Sam was hunched over the third page of the essay, editing mistakes in red pen. They'd spent the past three hours downstairs, eating dinner and watching a movie while their parents were gone. It was supposed to just be a nice, fun night, except Dean and Cas had barely stopped talking to each other over dinner to even _look_ at Sam or Jess, and then the movie was spent witnessing Dean trying to make love to Castiel with his eyes. He glanced up from the paper, raising his eyebrows.

"You see it too?"

"Their gayness is probably visible on the moon." 

Sam laughed, his happy expression making Jess smile in return. Putting her own page of the essay down, she scooted over and sat closer to him, eyes turning intense. She cleared her throat before continuing, trying to make herself seem as serious as possible. After all, love was an important matter. Even at age eighteen, it was _obvious_  that they were meant to be together. They'd been best friends since forever, and from what Sam had told Jess, Castiel was the only person that could tolerate Dean for extended periods of time. They were perfect for each other. 

"Sam, we have to get them together. They can't do it on their own." Her voice was solemn, and Sam burst out laughing.

"What? Seriously?"

"What's wrong with that plan?" 

"Jess, what would we even  _do?"_  

"We just set them up! We get them to go on a date without them knowing it. It's simple," Jess gently shook Sam's shoulder, trying to convince him that  _heck yeah this was a good plan._

"Have you  _met_ my brother? He's about as smart as a brick when it comes to relationships. They've practically been dating for months and they don't know."

She sighed, shoving her face into her hands. "If they would just  _talk_ to each other..." 

"But they won't. Maybe they'll figure it out eventually?" Sam gave her a hopeful look, but the determination in her eyes was clear.

"We have to help them. Love is not something that you can just  _hope_ that they figure out - sometimes you have to shove it in their face. Which is what we have to do. C'mon, I have ideas."

Sam groaned, but sat still and watched as Jess scribbled down her plans on the back of their rough draft. 

 

***

 

They spent two hours that night coming up with a plan, ending with five possible scenarios to try when Jess's parents came to pick her up. Sam wished that she could have spent the night - listening to Dean and Cas next door laughing their asses off until 3 AM wasn't the best feeling. He groaned, stepping out of bed and picking up the list from the floor. Number four was something he could do on his own:  _Lock them in a room and refuse to let them out. Preferably a very small space. Sexual tension will get the best of them._ He laughed at Jess's wording, shaking his head slightly and running his fingers through his too-long hair.

 _Yep. The pantry works,_ Sam thought, grinning as he folded the sheet of paper and shoved it in the drawer of his nightstand. 

He got dressed quickly, keeping on his comfy flannel pants and tossing a gray t-shirt over his head. Walking downstairs, he could hear bacon sizzling and eggs being cracked. The kitchen was already messy, a carton of eggs taken out and one apparently having shattered on the counter top. Cas was breaking them with immense concentration, Dean next to him at the stove. Pancake mix was in a bowl, a gallon of milk seemed to have been spilled onto the floor, and flour was covering Castiel's hair and Dean's shirt. The older Winchester was staring at the blue-eyed boy next to him with such adoration that Sam felt like he was intruding, almost - the whole thing was so _domestic_.

When Cas lifted a hand to brush some flour off of Dean's cheekbone, the look on his brother's face was making  _Sam_ feel embarrassed - there was a blush, plain to see under his white-dusted skin, and his eyes were opened so wide that Sam feared that Dean's eyes might pop out of his head. Sam groaned softly, running a hand over his face as he heard Dean stuttering and laughing nervously.  _How can he charm girls in under five minutes, but he can't even talk to the guy he likes? A guy that he's known since he was TEN?_ Sam realized that Jess was very much correct - sometimes, people just needed a push in the right direction. And right then, the correct direction was the pantry, a small room adjacent to the kitchen. 

"Hey, Dean?" Sam called out quietly, struggling not to laugh when Dean whipped around and nearly slipped on the milk puddle.

"Mornin', Sammy! What d'you think about pancakes and eggs?"

"And bacon," Castiel supplied, voice even rougher than usual from sleep. 

"He's right - and bacon!" Dean was smiling a little wider than necessary when talking about breakfast foods, and Sam thought about turning his brother around and just  _shoving_ him into Cas - they were close enough in height, so there had to be  _some_ chance of them kissing each other that way, right?

"I actually kinda want cereal. Cas, could you go get some for me?" Sam put on his best puppy dog eyes, Castiel nodding quickly and heading to the pantry. "They should be on the top shelf!"

"Sam, get your own fucking cereal. He's a guest." 

"He's practically lived here since you became friends. Besides, I'm tired." 

"Dean, I cannot locate the cereal boxes." Castiel called from the pantry, both Winchesters hearing muffled words and the shuffling of boxes and cans.

"For the love of - Cas, they're on the top shelf." Dean sounded exasperated, but there was still a soft smile on his face.

"I cannot find them." 

"Fucking - Sam, don't let the bacon burn," Quickly turning and walking over to the pantry, Dean stepped inside and instructed Castiel to look on the  _top_ top shelf, not just the top shelf. 

Dean started to curse loudly when he realized that Sam had also barred the pantry door, a chair stuck under the doorknob and bacon still sizzling on the stove. Sam grinned maniacally, tending to the food and cleaning up the kitchen. He heard some talking going on in the other room, but it stopped abruptly after several minutes; looking up from the stove, he stepped over to the door and removed the chair, waiting another second before opening it. Mentally preparing himself to see his brother madly kissing his best friend, Sam opened the door.

 

***

 

"Number four was a bust, Jess," Sam was lying down on his bed, phone pressed to his ear and geometry homework sprawling over his pillows.

"What?  _How?"_ Jess sounded about as incredulous as Sam had felt the moment he'd opened up the pantry. Nothing had happened - Dean and Cas had just hunkered down onto the floor, playing rock-paper-scissors over and over again. 

"It's like they're immune to common romance tropes, Jess. They were  _making breakfast in the kitchen,_ Jess! Breakfast!"

She sighed into the receiver, and Sam heard a slight rustling on the other end of the line. "Alright. What are the other options again?"

Sam took out the list, unfolding the crease and scanning the page. "Number two looks promising. You said that we should hire a ton of people to walk up to them in public and ask them if they're dating, or just tell them that they look cute together."

"They  _do_ look cute together, but I don't know how much money people would want. And that would only plant the idea in their heads, not really get them into action. What else is there?"

"Number five: 'spin the bottle. Put a magnet in Cas's pants.' Are all of these just stereotypical story ideas?"

"They're proven to work, Sam!"

"By romantic comedies. Not real people."

Jess sighed again, the rustling making itself known again. "Jess, what's that noise?"

"Huh? Oh, I'm just making the bed." She paused. "Wait - BEDS! SAM! BEDS!"

"Beds?"

" _BEDS!_  We just need to put them in a situation where they  _have_ to share a bed! Then they'll wake up cuddling, and maybe one of them will forget they're just friends and randomly kiss the other's cheek and - SAM! It's  _perfect!"_

"I think they already share a bed for sleepovers, Jess," Sam felt disappointment crawling up his spine, hating the way that Dean and Cas had to make this  _so fucking difficult._

"Check Dean's room! Look for a sleeping bag or sheets on the floor." 

"I'm not going into his room, Jess," He sighed, wondering how they could make this whole process easier. "I have to go. I'll call you back tomorrow, okay?"

"We have to finish this, Sam. Trust me. Have sweet dreams!" 

"Bye, Jess." 

 

***

 

A blessing came later that month in the form of a school dance, and Jess was struck with a genius plan. They'd tried a total of twelve different situations to try and get the two idiots together, but not a single one had worked. It was slow-going process, but Sam was having fun - he was getting to do it all with Jess. And when she came up with lucky number plan thirteen, even he had to admit it might work. It also involved having to slow-dance with his best friend that he also may have been falling head over heels for, but hey - this was all  _just_ for Castiel and Dean. 

They were going to the winter formal together, and Jess's plan was simple: tell Dean and Cas when they're having a dinner/movie night at the Winchester household, admit to having no idea how to dance, and forcing Dean and Castiel to show them how to due to faking complete incompetency in all things dance-related. When the night came for the plan to be carried out, Sam and Jess were practically bubbling over in excitement at dinner, anxiously waiting to succeed in matching two people together. 

Sam cleared his throat, gathering the attention of everyone. Dean and Cas had been mid-conversation, and Dean didn't look very pleased about being interrupted, but his expression changed to pride when Sam made his announcement. 

"Jess and I are going to the formal together."

Castiel nodded. "Congratulations, Sam. And you too, Jess."

Dean was beaming, reaching over the table to clap his brother on the back. "Way to go, Sammy!" He turned to Jess, fake-whispering. "You know you're way out of his league, right?"

Sam groaned, Jess laughing softly and looking at him.  _This_ was the important part - this next line, the next step in plan thirteen. 

"And we also don't know how to dance." Sam swallowed, glancing between his brother and Castiel. Cas's head was tilted slightly to the side, eyes squinting. Dean's face was one of pure disbelief. 

"I could teach you, Sam. The waltz is not difficult, although you might want to learn the tango if you both desire to be more flamboyant-"

"Jess, you're seriously telling me you can't dance?" Dean interrupted, face skeptical.

"Nope," she shrugged, looking to Sam and then back at the two boys across the table.

"Perhaps we could teach you." Castiel said, turning to Dean, who was sputtering and turning red as soon as the words left Cas's mouth.

_"What?"_

"We both know how to, Dean. It would not be difficult."

Dean visibly swallowed, turning over to Sam and Jess, younger kids nodding vigorously. "Fine. Only one dance."

They migrated to the living room, scooting the coffee table and two chairs out of the way to make room for a small dance floor. Sam and Jess stood next to each other, giddy with excitement. Everything was going the right way, Dean was fiddling with the speakers to play some music, Cas was instructing them on form, it was all  _working._ Dean finally put on some soft rock, soothing guitar chords filling the room. He stood next to Castiel, arms stiff at his sides and a blush apparent on his cheeks. When Castiel shifted around Sam and Jess, they could see that his cheeks were tinged pink, too.

"Sam, put one hand on her waist and the other here. Jess, step closer, you're supposed to be touching there - no, don't - Sam, that is incorrect-" 

"Why don't you just _show_ us?" Jess faked exasperation, stepping away in mock frustration and gesturing to Dean. "Demonstrate. Let us see. Cas, you be me. Dean, you be Sam." 

Dean looked affronted. "Why don't I get to be Jess?"

"Because I have better hips," Castiel quipped, Sam and Jess unable to control their laughter.

Dean turned a brighter shade of red, sticking out his hands so Castiel could get into position. He settled a hand on Cas's waist, and Sam couldn't help noticing the way Dean's hand almost  _caressed_ Castiel's side. They linked their other hands, Cas resting his fingers on Dean's shoulder. He turned to Jess, nodding at their position. "See? Correct form." 

Jess smiled slyly, and Sam grinned with her. "You said you have to be almost touching. You guys are still three feet apart."

The older boys looked down, seemingly unaware of the giant space between them. They moved closer, refusing to look at each other. Sam and Jess mirrored the position, slowly stepping to the music. Castiel occasionally offered a word about their posture or missing a beat, but otherwise, he just danced along with Dean. Sam was having so much fun with Jess that he didn't even notice Dean and Castiel until she pointed over to them on the opposite side of the room.

The two were quietly rocking, having abandoned correct form and instead practically  _cradling_ each other, simply swaying in place. The songs playing were now almost all soft and slow, and Jess pointed to the door of the room. Sam followed her, darting away from his brother and his hopefully soon-to-be-boyfriend. They quietly walked down the hall to Sam's room, shutting the door and deciding to celebrate their victory by jumping on the bed. After their brief bout of excitement, Jess sat on the edge of the mattress, holding Sam's hand gently. The sparks going up and down his arm felt amazing, and seeing the soft smile Jess gave him felt even better. 

"Do you think we should check on them? It's been twenty minutes," Jess asked, leading Sam to the door.

They padded down the hallway, music playing classical music. Sam couldn't help wondering why Dean  _had_ classical - he wasn't really a "soulful flute solo" kind of guy. But as they walked into the room, they saw something that Sam wanted to permanently erase from his memory. Dean was sitting on the couch, Castiel leaning over and kissing him in a way that looked  _far_ dirtier than what Sam thought Cas would be capable of. Jess turned around, covering her mouth and dragging Sam back out and down the hall, darting into his room once more.

"Success!" She said happily, throwing her arms over his shoulders and holding on tight.

"Yeah," Sam said softly, wrapping his arms around her waist. "Definitely a success." 

**Author's Note:**

> thanks for reading, hope you enjoyed!  
> feedback is appreciated~


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